(side 1) The southern portion of Whitfield Estates was developed on land originally owned (1876-1912) by Fannie and General John Riggin Jr., an aide-de-camp of General Ulysses S. Grant during the Civil War.

In 1924 a corporation led by Louis Broughton Whitfield of Montgomery, Alabama assembled 682 acres of land that included the 218 acre bayfront estate of the late Alfred Ringling. With a vision to create a town to rival Coral Gables, the master plan for Whitfield Estates included a majestic tourist hotel overlooking the bay, an 18-hole golf course, a business district, a yacht club, and the creation of islands in the bay.

Construction began in October 1924 an lots in the first unit (south of Whitfield Avenue) went on sale in January 1925. The phase north of Whitfield Avenue was platted in October 1925. The units east of the Tamiami Trail and the Donald Ross-designed golf course (now Sara Bay Country Club) were added in 1926.
Promoted by the Adair Realty and Trust Company as "the Jewel of the West Coast," Whitfield Estates was one of the most highly regarded development ventures during the 1920s Florida Land Boom.

(side 2) Legendary golfer Bobby Jones was the assistant sales manager and noted builders and architects included T.A. Monk and Ralph Twitchell. By the summer of 1926, an apartment building, 61 homes, a retail store, and the country club were completed or under construction.

In June 1926 Whitfield Estates incorporated as a town and elected its own mayor. Little did they know the Land Boom had already begun to dissolve and in March 1927 the developer filed for bankruptcy. Development halted and did not resume until the 1940s with the post-WWII housing boom. In 1949 Whitfield Estates established its own zoning district which existed until 1981 and ultimately led to the creation of the Whitfield Residential Overlay District.

The special character of Whitfield Estates is distinguished by a century of architectural styles which include many vintage homes built during one of Florida's most exciting eras.